AU2001290367B2 - Synthesis of ester linked long chain alkyl moieties - Google Patents
Synthesis of ester linked long chain alkyl moieties Download PDFInfo
- Publication number
- AU2001290367B2 AU2001290367B2 AU2001290367A AU2001290367A AU2001290367B2 AU 2001290367 B2 AU2001290367 B2 AU 2001290367B2 AU 2001290367 A AU2001290367 A AU 2001290367A AU 2001290367 A AU2001290367 A AU 2001290367A AU 2001290367 B2 AU2001290367 B2 AU 2001290367B2
- Authority
- AU
- Australia
- Prior art keywords
- cetyl
- aromatic hydrocarbon
- mixture
- acid
- myristate
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Ceased
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
- C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
- C11C3/003—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fatty acids with alcohols
Abstract
A process for preparing a mixture of cetyl myristate and cetyl palmitate comprising reacting both myristic and palmitic acid with cetyl alcohol with an acid catalyst and one aromatic hydrocarbon at an elevated temperature and recovering from the aromatic hydrocarbon fraction the cetyl myristate and cetyl palmitate.
Description
24-APR-2008 16:44 A J PARK 64 9 3096943 P.04 -1 00 o "SYNTHESIS OF ESTER LINKED LONG CHAIN ALKYL MOIETIES"
BACKGROUND
2 The present invention relates to synthesis of ester linked long chain alkyl ?i moieties. More particularly the present invention comprises an improved synthesis of cetyl ester and to products so synthesised.
Cetyl myristate and cetyl palmitate are useful in the formulation of cosmetics C and pharmaceuticals. More particularly, this invention in the synthesis of said cetyl myristate with required palmitate, relates more specially to improved synthesis yields N as well as more efficient removal of impurities in the process.
o The esters, cetyl myristate and cetyl palmitate are each currently marketed for O use in cosmetics and pharmaceuticals.
Cetyl myristate has been produced by an acid catalysed reaction of myristic acid with cetyl alcohol. Cetyl palmitate likewise has been produced by an acid catalysed reaction of palmitic acid with cetyl alcohol. Because of the purity requirements of the cosmetic and pharmaceutical industries each product so synthesised requires extensive and intensive purification procedures.
DESCRIPTION OF THE INVENTION In one aspect the present invention consists in a process for preparing a mixture of cetyl myristate and cetyl palmitate which comprises, reacting both myristic acid and palmitic acid with cetyl alcohol in the presence of at least one acid catalyst and at least one aromatic hydrocarbon at a temperature of from 65°C to 140°C, to form an aromatic hydrocarbon fraction containing cetyl myristate and cetyl palmitate, and (ii) recovering from the aromatic hydrocarbon fraction the cetyl myristate and cetyl palmitate.
Preferably the ratio of the reactants is substantially stoichiometric.
Preferably the acid catalyst is one that will predominate (preferably almost exclusively) in an aqueous fraction rather than that of said aromatic hydrocarbon.
Preferably said catalyst is phosphoric acid (preferably 85% phosphoric acid).
Preferably there is an aqueous fraction from which the aromatic hydrocarbon fraction is separated prior to recovering the cetyl myristate cetyl palmitate from the aromatic hydrocarbon fraction.
100030266 COMS ID No: ARCS-188129 Received by IP Australia: Time 14:47 Date 2008-04-24 24-APR-2008 16:44 A J PARK 64 9 309943 P.055 00 -2- 00 S Preferably substantially all of the catalyst is retained in the aqueous fraction.
SPreferably said aromatic hydrocarbon is of the benzene series and has from six to nine carbon atoms.
Preferably the aromatic hydrocarbon is toluene or xylene (or a mixture thereof).
Preferably the cetyl myristate comprises from about 50 to about 98% w/w of the mixture.
Preferably the recovering of cetyl myristate and cetyl palmitate is by crystallisation and recovery from the aromatic hydrocarbon.
In another aspect our invention comprises a process for preparing a mixture of cetyl myristate and cetyl palmitate, this process includes reacting cetyl alcohol Swith both myristic acid and palmitic acid admixed with an aromatic hydrocarbon C containing from 6 to 8 carbon atoms of the benzene series in the presence of phosphoric acid at an elevated temperature (65°C to 140°C) with agitation for several hours, preferably 8-45 hours. Preferably after the reaction is complete, the desired product is recovered from the aromatic liquid hydrocarbon. One preferred recovering procedure is crystallization and filtration. Alternatively, in another preferred procedure the aromatic liquid can be employed to continuously extract ester from the reaction mixture as the reaction is in progress.
One of the most preferred aspects of the present invention resides in the employment of aromatic non-miscible liquid hydrocarbon. The use of a solvent such as toluene or xylene is superior to any other solvent suggested by the prior art.
In still another aspect the invention consists in a mixture of cetyl myristate and cetyl palmitate produced by a process as previously defined.
In yet another aspect the invention consists in the use of such a mixture in the treatment of inflammatory ailment in a mammal or in a process to produce an oral pharmaceutical composition useful in the treatment of inflammatory ailments.
Preferably one such ailment is asthma.
Preferably the cetyl myristate comprises from about 50 to about 98% w/w of the mixture.
In still a further aspect the present invention consists in an oral composition for treating inflammatory ailments comprising or including both cetyl myristate and cetyl palmitate.
Preferably the composition comprises from 50 to 98% w/w of cetyl myristate with respect to the total weight of cetyl myristate and cetyl palmitate. Preferably the ailment is asthma.
100030266 COMS ID No: ARCS-188129 Received by IP Australia: Time 14:47 Date 2008-04-24 4-PR-208 16:44 A J PARK 64 9 3096943 P.06 O The term "comprising" as used in this specification and claims means "consisting at least in part of, that is to say when interpreting independent paragraphs including that term, the features prefaced by that term in each paragraph will need to be present but other features can also be present.
Experiment A.-Hexane Solvent Myristic acid palmitic acid, 200 cc. of 85% phosphoric acid and 1800 ml of Shexane were mixed, heated to reflux and then 251 grams of cetyl alcohol added in O min. The mixture was refluxed further for 8 hours. Then the hot mixture consisted of a muddy acid layer and a opaque solvent layer which could not be separated by o decantation or filtration. The mixture was further diluted with three volumes of hexane N causing the slushy hexane layer to further soften enough to be separated from aqueous layer. The hexane layer was then cooled to bring about crystallization of fatty ester. The weight of cetyl myristate isolated was 294 grams which had a melting point of 54-590C. The conversion, based on the cetyl alcohol used, was 63.71%.
Experiment B.-Heptane Solvent Myristic acid palmitic acid, 200 cc. of phosphoric acid, and 1800 ml. of heptane were mixed, heated to reflux and then 251 grams of cetyl alcohol refluxed further for 18 hours and separated as in example A. On crystallization, the cetyl myristate obtained was much darker in colour then in Experiment
A.
It is evident that this process as exemplified by Experiment B is even less satisfactory than that set forth in Experiment A.
Experiment C.-Alkylation in absence of a solvent Myristic acid palmitic acid, 400 cc. of 85% phosphoric acid were mixed, heated to 95 and 251 grams of cetyl alcohol was added over a period of 30 minutes. The mixture further heated in vacuum and then on cooling. The reaction mixture, which contained a finely divided white solid, was diluted to 3000 ml. with water cooled to C. and filtered. The white product was treated with hot water, and the mixture filtered hot to remove any alcohol.
The unreacted fatty acid was present in a large quantity. The reaction was not complete.
It is quite evident that the entire absence of a solvent in the process results in the complete failure to produce any substantial quantity of said ester.
The following example serves to illustrate the process of our invention in a manner as nearly identical as possible to the process of experiment A. In each of 100030266 COMS ID No: ARCS-188129 Received by IP Australia: Time 14:47 Date 2008-04-24 24-AR-2008 16:44 A J PARK 64 9 3096943 P.07 -4- 00 .t o Example 1 and Experiment A, the cetyl myristate was filtered from two litres of C Toluene. It is evident that the process employing toluene is far superior Example 1. -Toluene solvent 1800 cc. of toluene, myristic acid palmitic acid and 400 cc. of 85% phosphoric Sacid were mixed, heated to 920C. and 251 grams of cetyl alcohol was introduced over a 30-minute period. When the addition was complete, the reaction mixture was further refluxed for 38 hours, The hot reaction mixture was a two phase system CC consisting of a toluene layer and an aqueous phosphoric acid layer. No solid material o was present. The hot toluene layer was separated and mixed with charcoal to remove CN the undesired colouring matter.
SThe filtrate was cooled to bring about crystallization of cetyl myristate which was O isolated by filtration. The weight of cetyl myristate isolated was 436 grams which had a melting point of 54-58°C. The percentage conversion based on the cetyl alcohol employed was 92.3 percent.
The following example serves to illustrate the employment of xylene as the solvent, otherwise similar to Example 1 given above: Example Xvlene solvent Myristic acid palmitic acid, 250 grams of 85% phosphoric acid and 1000 cc. of xylene were mixed in a three neck flask provided with thermometer, agitator and reflux condenser. The temperature was increased to 105 with good agitation and grams of cetyl alcohol was introduced over a one-hour period. After the reaction the supernatant xylene layer was drawn off, and the lower phosphoric acid layer was preserved for use in the following run.
The xylene layer on cooling deposited a crystalline solid which weighed 154 gms. This material consisted of cetyl myristate and any unreacted fatty acid. The crude product was easily purified by recrystallization from hot xylene to yield pure cetyl myristate M.P.=54-56 0
C.
The process of our invention as exemplified by examples 1 and 2 involves the reaction of approximately equimolecular proportions of fatty acid and cetyl alcohol in order to accomplish the most advantageous results. However, higher and lower proportions within the vicinity of ratio of 1:1 can be employed.
The solvent which is employed in accordance with our invention is most advantageously toluene or xylene although other aromatic hydrocarbons of the benzene series containing from six to eight or nine carbon atoms can be employed.
The catalyst employed in accordance with our invention is most advantageously 100030266 COMS ID No: ARCS-188129 Received by IP Australia: Time 14:47 Date 2008-04-24 24-APR-2008 16:44 F J PARK 64 9 3096943 P.08 00 O phosphoric acid; however, other acid catalysts can be employed. The use of 85% S phosphoric acid is advantageously employed in the various examples given; however, equivalent quantities of other strengths of phosphoric acid can also be employed.
The elevated temperature employed in accordance with our process is most advantageously that at which reflux conditions exist. With proper stirring, temperatures which are higher or lower than that by reflux can also be employed.
t (temperature of from about 65 to about 1401C. can be advantageously employed) SThe following example will serve to illustrate this aspect of our invention: SExample 3. Xylene solvent Myristic acid palmitic acid, 400 cc. of 85% phosphoric acid and 2400 cc. of Sxylene were mixed in a three neck flask provided with a thermometer, agitator and reflux condenser. The temperature was raised to 1051C. with good agitation and 251 grams of cetyl alcohol was introduced with good agitation over a 1-hour period. The mixture refluxfor 36 hour. Next, the supernatant xylene layer was drawn off, and the lower phosphoric acid layer was preserved for use in a subsequent run. The xylene layer on cooling deposited a crystalline solid which weighed 438 grams. This crude material was substantially cetyl myristate and was purified by recrystallization from hot xylene so as to yield pure cetyl myristate having a melting point of 54-560C.
The water which is formed by the employment of cetyl alcohol in the course of the reaction as in Example 2 dilutes the reaction mixture but can be readily removed by azeotropic distillation of the reaction mixture.
In addition to the procedure illustrated by Examples 1,2 and 3, a successful batch process can be advantageously employed for preparing cetyl myristate with adequate palmitate which comprises, admixing under reflux conditions about one mole proportion of fatty acid Sfrom about 1 to about 5 times the same weight of phosphoric acid and from about 1 to about 2 times the same weight of an aromatic hydrocarbon containing from 6 to 8 carbon atoms, maintaining this admixture at its boiling point under good agitation and gradually introducing into this admixture about one mole proportion cetyl alcohol while substantially concurrently removing water by azeotropic distillation, i 100030266 COMS ID No: ARCS-188129 Received by IP Australia: Time 14:47 Date 2008-04-24 24-APR-2008 16:45 A J PARK 64 9 3096943 P.09 -6- 00 o thereafter separating while hot the layer containing the principal part of the aromatic hydrocarbon from the layer containing the phosphoric i acid, then cooling this layer whereby a product consisting primarily of cetyl i ,myristate separates as crystals, and admixing under refluxed condition for 38 hours.
i-i 0.
IIN
100030266 COMS ID No: ARCS-188129 Received by IP Australia: Time 14:47 Date 2008-04-24
Claims (9)
- 4-PR-2008 16:45 A J PARK 64 9 3096943 -7- 0 CLAIMS: N 1. A process for preparing a mixture of cetyl myristate and cetyl palmitate which comprises, reacting both myristic acid and palmitic acid with cetyl alcohol in the Spresence of at least one acid catalyst and at least one aromatic hydrocarbon, at a temperature of from 65°C to 140C, to form an aromatic hydrocarbon fraction containing cetyl myristate and cetyt palmitate, and n (ii) recovering from the aromatic hydrocarbon fraction the cetyl myristate and cetyl palmitate. C 2. A process of claim 1 wherein the ratio of the reactants is substantially o stoichiometric. C 3. A process of claim 1 or 2 wherein the acid catalyst is one that will predominate in an aqueous fraction rather than that of said aromatic hydrocarbon. 4. A process of claim 3 wherein the acid catalyst will predominate almost exclusively in an aqueous fraction. A process of any one of the preceding claims wherein said catalyst is phosphoric acid.
- 6. A process of claim 5 wherein said catalyst is 85% phosphoric acid.
- 7. A process of any one of the preceding claims wherein there is an aqueous fraction from which the aromatic hydrocarbon fraction is separated priorto recovering the cetyl myristate and cetyl palmitate from the aromatic hydrocarbon fraction.
- 8. A process of claim 7 wherein substantially all of the catalyst is retained in the aqueous fraction.
- 9. A process of any one of the preceding claims wherein said aromatic hydrocarbon is of the benzene series and has from six to nine carbon atoms. A process of claim 9 wherein the aromatic hydrocarbon is toluene or xylene or a mixture thereof.
- 11. A process of any one of the preceding claims wherein the cetyl myristate comprises from about 50 to about 98% w/w of the mixture.
- 12. A process of any one of the preceding claims wherein the recovering of cetyl myristate and cetyl palmitate is by crystallisation and recovery from the aromatic hydrocarbon.
- 13. A process for preparing a mixture of cetyl myristate and cetyl palmitate, wherein the process includes reacting cetyl alcohol with both myristic acid and palmitic acid admixed with at least one aromatic hydrocarbon containing from 6 to 8 100030265 COMS ID No: ARCS-188129 Received by IP Australia: Time 14:47 Date 2008-04-24
- 24-APR-2008 16:45 A J PARK 64 9 3096943 P.11 00 o carbon atoms of the benzene series in the presence of phosphoric acid at a temperature of from 65°C to 140 0 C with agitation for several hours and recovering the Smixture from the aromatic liquid hydrocarbon(s). 14. A process of claim 13 wherein the agitation is from 8 to 45 hours. c 15. A process of claim 13 or 14 wherein recovery is by crystallization and filtration. 16. A process of claim 13 or 14 wherein the recovery of the esters is whilst reaction continues. 17. A process for preparing cetyl myristate and cetyl palmitate when performed o substantially as hereinbefore described with reference to any of the examples. 18. A mixture of cetyl myristate and cetyl palmitate produced by a process as claimed in any one of the preceding claims. o 19. A mixture of claim 18 wherein the cetyl myristate comprises from about 50 to about 98% w/w of the mixture. i It 100030266 COMS ID No: ARCS-188129 Received by IP Australia: Time 14:47 Date 2008-04-24
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/NZ2001/000179 WO2003018731A1 (en) | 1998-11-23 | 2001-08-31 | Synthesis of ester linked long chain alkyl moieties |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU2001290367A1 AU2001290367A1 (en) | 2003-06-05 |
| AU2001290367B2 true AU2001290367B2 (en) | 2008-06-19 |
Family
ID=32227913
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2001290367A Ceased AU2001290367B2 (en) | 2001-08-31 | 2001-08-31 | Synthesis of ester linked long chain alkyl moieties |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US7411079B2 (en) |
| EP (1) | EP1421161B1 (en) |
| AT (1) | ATE399836T1 (en) |
| AU (1) | AU2001290367B2 (en) |
| CA (1) | CA2459087C (en) |
| CY (1) | CY1109384T1 (en) |
| DE (1) | DE60134675D1 (en) |
| ES (1) | ES2309092T3 (en) |
| HK (1) | HK1065815A1 (en) |
| WO (1) | WO2003018731A1 (en) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20030153620A1 (en) * | 2000-05-12 | 2003-08-14 | Meakin Timothy David | Treating eczema and/or psoriasis |
| NZ533370A (en) | 2004-06-03 | 2006-11-30 | Meracol Corp Ltd | Use of cetyl myristate and cetyl palmitate in therapy for multiple sclerosis |
| WO2006092605A1 (en) * | 2005-03-02 | 2006-09-08 | Croda International Plc | Compounds |
| EP2583673A1 (en) | 2010-10-14 | 2013-04-24 | Deva Holding Anonim Sirketi | Coating of cetyl myristate and/or cetyl palmitate particles |
| EP2543364A1 (en) | 2010-10-14 | 2013-01-09 | Deva Holding Anonim Sirketi | Formulations of cetyl myristate and/or cetyl palmitate |
| EP2441441A1 (en) | 2010-10-14 | 2012-04-18 | Deva Holding Anonim Sirketi | A sieving method for cetyl myristate and/or cetyl palmitate |
| EP2441446A1 (en) | 2010-10-14 | 2012-04-18 | Deva Holding Anonim Sirketi | Using of superdisintegrants in cetyl myristate and/or cetyl palmitate formulations |
| EP2471384A1 (en) | 2010-12-29 | 2012-07-04 | Deva Holding Anonim Sirketi | Suspension formulations of cetyl myristate and/or cetyl palmitate |
| EP2471514A1 (en) | 2010-12-29 | 2012-07-04 | Deva Holding Anonim Sirketi | Controlled moisture content of cetyl myristate and/or cetyl palmitate granules or formulations |
| EP2471386A1 (en) | 2010-12-29 | 2012-07-04 | Deva Holding Anonim Sirketi | Cetyl myristate and/or cetyl palmitate suspension formulations |
| EP2471387A1 (en) | 2010-12-29 | 2012-07-04 | Deva Holding Anonim Sirketi | Cetyl myristate and/or cetyl palmitate suspension formulations |
| EP2471385A1 (en) | 2010-12-29 | 2012-07-04 | Deva Holding Anonim Sirketi | Cetyl myristate and/or cetyl palmitate suspension formulations |
| EP2471528A1 (en) | 2010-12-29 | 2012-07-04 | Deva Holding Anonim Sirketi | A preparation method for suspension of cetyl myristate and/or cetyl palmitate |
| EP2526931B1 (en) | 2011-05-23 | 2014-12-17 | Deva Holding Anonim Sirketi | Wet granulation methods of cetyl myristate and/or cetyl palmitate |
| ES2538079T3 (en) | 2011-05-23 | 2015-06-17 | Deva Holding Anonim Sirketi | Particle size distribution of cetyl myristate and / or cetyl palmitate |
| ITUB20153130A1 (en) * | 2015-08-14 | 2017-02-14 | Pharmanutra S P A | Cetylated fatty acids, plant for their preparation and their use |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB756549A (en) * | 1952-10-15 | 1956-09-05 | Schou Herbert | Aqueous dispersions of water-insoluble fatty acid esters |
| US4049824A (en) * | 1976-05-03 | 1977-09-20 | Harry Weldon Diehl | Cetyl myristoleate |
| US5219733A (en) * | 1985-03-06 | 1993-06-15 | Yoshikawa Oil & Fat Co., Ltd. | Process for preparing fatty acid esters |
| US4654207A (en) * | 1985-03-13 | 1987-03-31 | Helene Curtis Industries, Inc. | Pearlescent shampoo and method for preparation of same |
| FR2717731B1 (en) * | 1994-03-24 | 1996-05-15 | Chryso Sa | Concentrate for demolding emulsion of hydraulic binders, demolding emulsion and use. |
-
2001
- 2001-08-31 ES ES01970366T patent/ES2309092T3/en not_active Expired - Lifetime
- 2001-08-31 AT AT01970366T patent/ATE399836T1/en active
- 2001-08-31 AU AU2001290367A patent/AU2001290367B2/en not_active Ceased
- 2001-08-31 EP EP01970366A patent/EP1421161B1/en not_active Expired - Lifetime
- 2001-08-31 CA CA2459087A patent/CA2459087C/en not_active Expired - Fee Related
- 2001-08-31 WO PCT/NZ2001/000179 patent/WO2003018731A1/en active Application Filing
- 2001-08-31 DE DE60134675T patent/DE60134675D1/en not_active Expired - Lifetime
- 2001-08-31 US US10/488,028 patent/US7411079B2/en not_active Expired - Fee Related
-
2004
- 2004-11-05 HK HK04108726A patent/HK1065815A1/en not_active IP Right Cessation
-
2008
- 2008-09-29 CY CY20081101069T patent/CY1109384T1/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ES2309092T3 (en) | 2008-12-16 |
| EP1421161A4 (en) | 2005-03-02 |
| ATE399836T1 (en) | 2008-07-15 |
| US20050033070A1 (en) | 2005-02-10 |
| WO2003018731A1 (en) | 2003-03-06 |
| DE60134675D1 (en) | 2008-08-14 |
| US7411079B2 (en) | 2008-08-12 |
| EP1421161A1 (en) | 2004-05-26 |
| CA2459087C (en) | 2011-04-19 |
| CY1109384T1 (en) | 2014-07-02 |
| CA2459087A1 (en) | 2003-03-06 |
| HK1065815A1 (en) | 2005-03-04 |
| EP1421161B1 (en) | 2008-07-02 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| AU2001290367B2 (en) | Synthesis of ester linked long chain alkyl moieties | |
| AU2001290367A1 (en) | Synthesis of ester linked long chain alkyl moieties | |
| JPS6233223B2 (en) | ||
| NZ332959A (en) | Preparation of cetyl myristate and cetyl palmitate | |
| WO2023170048A1 (en) | Crystallization of 4-hydroxyacetophenone from ethanol and ethyl acetate | |
| EP1041080B1 (en) | Process for the preparation of pentaacetyl-beta-D-glucopyranose | |
| JPH10500941A (en) | Purification of amidocarboxylic acid | |
| US6278014B1 (en) | Synthetic procedure for the manufacture of aspirin | |
| JP2618433B2 (en) | Purification method of crude 4-aminophenol | |
| JPS6210510B2 (en) | ||
| CN101096356B (en) | Purification technique of 9-fluorenylmethoxycarbon succinimide ester | |
| JPS6034558B2 (en) | Method for producing N,N'-bis-trimethylsilyl urea | |
| US3268566A (en) | Process for the production of tetramethyl titanate | |
| JPS6244538B2 (en) | ||
| UA77292C2 (en) | A process for the preparation of zaleplon | |
| JPS5885843A (en) | Preparation of succinylsuccinic diester | |
| JPH0273033A (en) | Production of 4, 4-dimethyl-1-(p-chlorophenyl) pentane-3-one | |
| US3948972A (en) | Esterification of nitrobenzoic acids | |
| JP3312811B2 (en) | Method for purifying trans-1,4-cyclohexanedimethanol dialkyl sulfonate | |
| JPH0327342A (en) | Production of shikonin | |
| CN116375562A (en) | Refining method for preparing isoborneol by camphene hydration | |
| JPS6252754B2 (en) | ||
| JPS63227563A (en) | Isomerization of cyclic terpene compound | |
| JPS6312462B2 (en) | ||
| JPH0368571A (en) | Production of n-substituted 2,4,6-triiminotriazine derivative |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PC1 | Assignment before grant (sect. 113) |
Owner name: MERACOL CORPORATION LIMITED; JHAVERI, PARAG Free format text: FORMER APPLICANT(S): JHAVERI, PARAG; CADWALLADER, DIANNE |
|
| PC1 | Assignment before grant (sect. 113) |
Owner name: MERACOL CORPORATION LIMITED Free format text: FORMER APPLICANT(S): MERACOL CORPORATION LIMITED; JHAVERI, PARAG |
|
| FGA | Letters patent sealed or granted (standard patent) | ||
| PC | Assignment registered |
Owner name: LYPANOSYS PTE LIMITED Free format text: FORMER OWNER WAS: MERACOL INVESTMENTS LIMITED Owner name: MERACOL INVESTMENTS LIMITED Free format text: FORMER OWNER WAS: MERACOL CORPORATION LIMITED |
|
| MK14 | Patent ceased section 143(a) (annual fees not paid) or expired |